Tetrahedron p. 2297 - 2302 (1984)
Update date:2022-09-26
Topics:
Chamberlin, A. Richard
Mulholland, Robert L.
Reaction of electrophiles with a variety of acyclic allylic alcohols was investigated.Both aqueous iodine and acetylhypoiodite convert certain alkenols into iodo diols and acetoxy iodo alcohols, respectively, with regio- and stereoselectivities as high as 99percent.Protection of alcohol group lowers the selectivity only slightly.Structural factors that control the regioselectivity of iodohydrin formation in these substrates have been delineated.Some of the iodo diols have been deiodinated, illustrating a simple two step procedure for converting allylic alcohols into threo-1,3-diols.
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